About Where Leadership Matters Podcast: Technology
Our world is evolving immeasurably. Having the right leadership has never been more crucial. Welcome to ‘Where Leadership Matters,’ a podcast series that dives into pivotal career moments and high-stakes decisions across the tech industry. Each episode brings you insights from top business leaders around the globe, sharing their expertise on leadership, innovation, and strategic decision-making. Tune in to explore a wide array of topics and gain invaluable perspectives from global industry experts.
Beyond Functions: How AI is Transforming Organizations
Rupert Lion, Partner in Odgers' Technology Practice and Head of Scale Up Collective at Odgers US, sits down with Deborah Kops, global business services and governance leader, to explore how AI is reshaping organizational design, work, and capabilities.
The conversation delves into the evolving role of corporate functions, the distinction between skills and capabilities, and the potential for AI to act as a force multiplier rather than just a productivity tool. Deborah and Rupert discuss the future of operating models, the disintermediation of traditional workflows, and the transformation of consulting, employment structures, and corporate boards in an AI-driven world. They also examine the cultural and strategic challenges organizations face in adopting AI, from trust and speed of change to the need for more fluid and outcome-oriented workforce models.
This episode offers a provocative look at how AI could fundamentally change the way organizations operate, drive outcomes, and rethink the relationship between people, work, and enterprise.
3 Dec 2025
AI in the Enterprise: Leadership, Transformation, and the Future of Work
Rupert Lion, Partner in Odgers' Technology Practice and Head of Scale Up Collective at Odgers US, sits down with Jim Kaskade, CEO of Conversica and seasoned Silicon Valley AI leader, to explore how AI is transforming enterprise technology, leadership, and workforce strategy.
The conversation delves into the practical challenges of deploying AI at scale, the evolution of large language models, and the balance between probabilistic systems and deterministic decision-making in real-world applications. Jim and Rupert discuss how AI is reshaping roles across sales, engineering, and customer service, the implications for workforce reskilling, and the critical role of leaders in driving adoption and fostering AI literacy.
They also examine the broader enterprise landscape, including how organizations navigate risk, governance, and investment in AI, and what it takes to turn emerging technologies into sustainable competitive advantage. This episode offers an insightful look at the intersection of AI, leadership, and organizational transformation, and what it means for the future of enterprise innovation.
11 Sept 2025
The AI Shift: Redefining Business, Work, and Trust
Rupert Lion, Partner in Odgers' Technology Practice and Head of Scale Up Collective at Odgers US, sits down with Serena Dayal, Serial Board Member and Ex-Softbank Partner, to explore how AI is redefining business, work, and trust.
The conversation dives into the evolving role of proprietary data, the future of skills-based hiring, and the emergence of AI-powered co-workers. Serena and Rupert discuss the shifting dynamics of trust between humans and intelligent agents, the transformation of marketing and search, and the implications of AI for consumer applications, autonomous vehicles, and supply chains. They also tackle the ethical and regulatory challenges posed by AI, and the potential for collaboration between enterprise, academia, and government to solve humanity’s biggest problems.
This episode offers a thought-provoking look at the seismic changes AI is bringing to business, work, and society and what it means for the future of innovation and leadership.
28 Jul 2025
AI with Sight and Insight: Chooch AI’s Vision for the Future
Join Rupert Lion, Partner in Odgers' Technology Practice and Head of Scale Up Collective US, as he sits down with Anubhav Saxena, CEO of Chooch AI, to explore the cutting edge of visual AI and computer vision. From his early days in defense research to leading one of the most innovative AI companies today, Saxena shares how AI is evolving beyond text to interact with the physical world.
Anubhav highlights how breakthroughs in compute power, economic feasibility, and the rise of frontier models have propelled AI forward—moving beyond text-based systems to what he calls “world AI,” where intelligence is applied to physical vision and real-world tasks.
Looking ahead, Anubhav predicts that AI will accelerate the “circle of life” in technology—from offshoring to automation to intelligent onshoring. While humanoid robots may become more common, he stresses the importance of economic viability and human-centric design in shaping the future of AI.
8 May 2025
The Future of Marketing: AI, Ads & Creativity
Join Rupert Lion, Partner in Odgers Berndtson's Technology Practice and Head of Scale Up Collective US, as he sits down with Steve Dunlop, an audio visionary and founder of AMA, a groundbreaking platform that transforms digital audio advertising through real-time, data-driven personalization, as they delve into the evolution of AI in advertising.
Rupert & Steve explore the role of human voice actors in AI-generated ads, future trends in audio advertising and how AI can boost creativity and efficiency in advertising while addressing market readiness challenges and the necessity for customized AI solutions. They explore AI's dual role in lead generation, the need for human oversight, and the future implications of AI development, balancing optimism with caution regarding its rapid progression.
1 Apr 2025
AI in Management: Leadership Insights
Join Rupert Lion, Partner in Odgers Berndtson's Technology Practice and Head of Scale Up Collective US as he sits down with Randy Bean, a veteran in AI and data-driven leadership and Author of ‘Fail Fast: Learn Faster’, to explore the dynamic landscape of artificial intelligence.
Rupert & Randy delve into the evolution of AI, the transformative impact of generative AI, and the latest trends in AI adoption among Fortune 1000 companies. Randy offers valuable insights from his annual survey, shedding light on the cultural hurdles organizations encounter in their journey to become data and AI-driven. The discussion also covers the emerging role of Chief AI Officers and the future of AI, stressing the importance of responsible AI practices and the need for cultural shifts within companies.
15 Jan 2025
E-Commerce Evolution: The AI Advantage
A discussion with Giles Whiting, CEO of parcelLab, interviewed by Rupert Lion, Partner in Odgers Berndtson's Technology Practice and Head of Scale Up Collective US.
Giles Whiting, the current CEO of parcelLab, the leading global provider of post-purchase experience software for online retailers. Throughout his career, Giles has excelled as an executive, investor, and advisor in some of the leading global SaaS companies of the past decades. In this episode, Rupert discusses with Giles how he leverages AI to create first-class customer journeys at parcelLab. They dive deep into the benefits of AI for the brands parcelLab works with, the complexities AI presents for retailers, and how parcelLab focuses on driving better customer experiences that ultimately increase loyalty and customer lifetime value.
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